Hillsdale Vacations

Book a Hotel + Flight or Car together to unlock savings

Your Hillsdale Vacation

There's no better way to get away than with one of our vacation packages to Hillsdale. The rich history and welcoming locals are just two of the convincing reasons you'll want to stay in this captivating city. When the time comes to go out and explore, be sure to put Taconic State Park and Catamount Aerial Adventure Park on the itinerary for your trip to Hillsdale. A couple of clicks is all it takes to craft the perfect Hillsdale vacation on Expedia.

Hillsdale Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Lake Taghkanic State Park, Hudson Chatham Winery and Catamount Aerial Adventure Park

Hillsdale Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $119 per night from Jun 9 to Jun 10
$119
$133 total
includes taxes & fees
Jun 9 - Jun 10
9/10 Wonderful! (253 reviews)
"Terrific renovation of two story motel. Great bedding and toiletries. Everything has a curated retro-hipster look. Spacious shower and bathroom, closet space, robes, plenty of charging outlets and a big TV, great if you use Apple. The only downside is noisy, bulky air conditioner. Be sure to ask ..."

Reviewed on May 28, 2024

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $128 per night from Jun 12 to Jun 13
$128
$142 total
includes taxes & fees
Jun 12 - Jun 13
9/10 Wonderful! (1,005 reviews)
Great place to stay
"The staff was super friendly. The room was clean and I had no issues at all."

Reviewed on Jun 4, 2024

The Yankee, Trademark Collection by Wyndham
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is $153 per night from Jun 17 to Jun 18
$153
$194 total
includes taxes & fees
Jun 17 - Jun 18
8.8/10 Excellent! (890 reviews)
"Always a great HISTORIC INN"

Reviewed on Jun 2, 2024

The Red Lion Inn
See all 1,687 properties in Hillsdale
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Hillsdale vacation package cost?
Explore the best of Hillsdale from as low as . Choose from a great selection of rental cars, hotels and flights to suit your budget. You can pick up even better deals when you add some tours or activities to your vacation package.
How do I get a cheap travel package to Hillsdale?
Our Hillsdale vacation packages offer plenty of savings for the savvy explorer. For the best deals, simply combine your flights, hotels and tours into a handy package. But great bargains are just the beginning of your next memorable adventure. When you book with Expedia, you’ll have more than 550 airlines and 1,000,000 hotels globally to choose from. No matter your style or budget, there’s a vacation package with your name on it.
Where should I stay in Hillsdale?
Hillsdale is home to a number of terrific places to see, like Catamount Aerial Adventure Park. Stay someplace near this attraction and make sightseeing easier.
What are the top hotels in Hillsdale?
If this will be your first time in Hillsdale, reserve a room at Cabin - Ideal Location For Summer And Winter Activities With Plenty Of Outdoor Space or Holiday House Motel Hillsdale. Both hotels will make you feel at home and are favorites with many savvy travelers.
How far in advance should I book my Hillsdale vacation?
Reward yourself with the biggest variety and the lowest prices by booking your Hillsdale adventure early. Air carriers typically release tickets anywhere up to 12 months prior to departure, so start your planning as soon as you can. That said, Expedia is constantly working to give you the best deals around, so it’s always a good time to book your dream vacation!
What does an Expedia Hillsdale travel package include?
Choose from a combination of rental cars, hotels and flights. Once you’ve made your booking, you can add experiences and tours. Want to pick your fare class? That’s easy to do too. The choice is all yours when it comes to planning your perfect Hillsdale getaway.
What should I know before booking a Hillsdale travel package?
An Expedia travel package can be tailored to your budget and is a terrific way to make your budget go further. What you include is up to you. Rental cars, hotels and flights — mix and match whatever combination suits your style.
Can I choose my airline with a Hillsdale Expedia vacation package?
Yes — that’s the beauty of an Expedia vacation package. You’re in charge! We have more than 550 airline partners around the world, so you have loads of choice when arranging your Hillsdale escape.
If I'm not able to travel, can I cancel my Hillsdale vacation package?
Whether it’s your hotel, flight or rental car, you can cancel or alter it. Booked your Hillsdale vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For more details, head to our Customer Service Portal. We’re here to help you each step of the way.

Discover the most popular places to visit in Hillsdale

Image for Catamount Aerial Adventure Park

Catamount Aerial Adventure Park

You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.

Catamount Aerial Adventure Park
Image for Community Library

Community Library

Community Library is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.

Community Library
Image for Hillsdale Town Hall

Hillsdale Town Hall

Hillsdale Town Hall is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.

Hillsdale Town Hall

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.